Sodium hydride → Ethyl 2-methoxymethyl-1-(2-trimethylsilylethoxymethyl)-1H-pyrrol-3-carboxylate

HRID 2097484Notes

Reaction equation

HRID 2097484 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][C:6]1[NH:7][CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[CH3:16][Si:17]([CH3:24])([CH3:23])[CH2:18][CH2:19][O:20][CH2:21]Cl.S([O-])(O)(=O)=O.[K+]>CN(C)C=O>[CH3:3][O:4][CH2:5][C:6]1[N:7]([CH2:21][O:20][CH2:19][CH2:18][Si:17]([CH3:24])([CH3:23])[CH3:16])[CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 66602591ethyl 2-(methoxymethyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 66602692Ethyl 2-methoxymethyl-1-(2-trimethylsilylethoxymethyl)-1H-pyrrol-3-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1250 ml of dehydrated N,N-dimethylformamide solution containing 63.1 g (1.45 mol) of sodium hydride (55% dispersed material in mineral oil) which had been washed three times with each 500 ml of dehydrated heptane was added dropwise 750 ml of dehydrated N,N-dimethylformamide solution containing 263 g (purity: 95%, 1.36 mol) of ethyl 2-methoxymethyl-1H-pyrrol-3-carboxylate obtained in Reference example 15-(c) at room temperature under argon atmosphere, and the mixture was stirred for 30 minutes. Then, 242 g (1.45 mol) of (2-trimethylsilylethoxy)methyl chloride was added dropwise to the mixture under ice-cooling, and the mixture was further stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was poured into ice-water, neutralized with 30% aqueous potassium hydrogen sulfate solution, and extracted with toluene. The organic layer after separation was washed successively with water, and then, with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 420 g (purity: 98.6%) of the title compound as a yellowish oil. (Yield: 96%)

Workup

  1. washhad been washed three times with each 500 ml of dehydrated heptane
  2. additionwas added dropwise 750 ml of dehydrated N,N-dimethylformamide solution
  3. customobtained in Reference example 15-(c) at room temperature under argon atmosphere
  4. temperaturecooling
  5. stirringthe mixture was further stirred at room temperature for 3 hours
  6. customAfter completion of the reaction
  7. extractionextracted with toluene
  8. customThe organic layer after separation
  9. washwas washed successively with water
  10. dry with materialwith a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-90bc742cb8c8416cb8a1ff0ffca2505a
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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